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I would simply replace the pages content as required. If the site is popular (PR in Googles eyes) Googlebot will visit each day and update accordingly.
www.website.com/listings/*listingidnumber*
So when the listing is sold, off the market, expired, etc. it is no longer linked from anywhere else on the website. In essence, it is outdated data.
Would it be better to just mark the listing as SOLD and let it sit in Google's database for eternity or would it be better to feed some type of 404 or 301 to prevent spamming up Google with outdated pages? (goin for the good karma here if possible)
/listings/31 - This property gets sold
I put a 301 redirect on that page to a page showing all listings:
/listings/31 -> 301 code -> /listinglist
Google has both urls already in the database:
GOOGLE RESULTS:
/listings/31 : Property Listing - 123 Main Street
/listinglist : Available Property List
After applying the 301, would Google still show this in a search:
/listings/31 : Available Property List (because this URL was redirected to /listinglist)
/listinglist : Available Property List
or would it drop the first listing and only leave the one that it was redirected to (which was already in Google's DB)?